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Acetohydroxamic acid

From Wikipedia, the free encyclopedia
An enzyme inhibitor that inhibits urease and thus can treat some infections
Pharmaceutical compound
Acetohydroxamic acid
Clinical data
Trade namesLithostat
AHFS/Drugs.comConsumer Drug Information
ATC code
Identifiers
  • N-Hydroxyacetamide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.008.104Edit this at Wikidata
Chemical and physical data
FormulaC2H5NO2
Molar mass75.067 g·mol−1
3D model (JSmol)
  • O=C(NO)C
  • InChI=1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) checkY
  • Key:RRUDCFGSUDOHDG-UHFFFAOYSA-N checkY
  (verify)

Acetohydroxamic acid (also known asAHA or by the trade nameLithostat) is adrug that is a potent and irreversibleenzyme inhibitor of theurease enzyme in variousbacteria andplants; it is usually used forurinary tract infections. The molecule is similar tourea but is nothydrolyzable by urease;[1] it thus disrupts the bacteria'smetabolism throughcompetitive inhibition.

Orphan drug

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In 1983 the USFood and Drug Administration approved acetohydroxamic acid (AHA) as anorphan drug for "prevention of so-calledstruvite stones" under the newly enactedOrphan Drug Act of 1983.[2] AHA cannot be patented because it is a standard chemical compound.[2]

See also

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References

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  1. ^Fishbein WN, Carbone PP (June 1965)."Urease Catalysis. Ii. Inhibition of the Enzyme by Hydroxyurea, Hydroxylamine, and Acetohydroxamic Acid".The Journal of Biological Chemistry.240:2407–14.doi:10.1016/S0021-9258(18)97338-2.PMID 14304845.
  2. ^abMarwick C (July 1983). "New drugs selectively inhibit kidney stone formation".JAMA.250 (3):321–2.doi:10.1001/jama.1983.03340030003001.PMID 6854890.
Urologicals, including antispasmodics (G04B)
Acidifiers
Urinaryantispasmodics
(primarilyantimuscarinics)
Other urologicals
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